Coating composition



50 pheres.

Patented Apr. 30, 1935 UNITED STATES 1,999,s 12 g I COATING COMPOSITION" Irvin Humphrey, .Wilmington, DeL, assignor to Hercules Powder Company, Wilmington, DL,

a corporation of Delaware- No Drawing. gori ginalapplication m; s, 1931,

Serial No. 541,953.

Divided and this application April13, IQSZQSerial No.605,120 9 Claims. (01. B l -'79) This invention relates to hydrogenated methyl abietate and to a novel method for its production The hydrogenated methyl abietate in accordance with this invention will be found toflbe a product lending itself to wide and varied use-in the commercial arts, as a high boiling ester of excellent solubility characteristics for use in protective coatings, as a non-drying oil, etc.

The hydrogenated methyl abietate in accordance with'this invention may be prepared by the hydrogenation of methyl abietate prepared in any suitable manner by the esterification of abietic acid, as such or as found in, for example, rosin.

In proceeding in accordance with this invention, methyl abietate is hydrogenated by treatment with hydrogen in the presence of an active nickel hydrogenation catalyst under suitable temperature, say 140 C. to 250 C., or preferably 150 C. to 200 C. and under a pressure of about 10-500 atmospheres, or preferably say 15-100 atmospheres. In effecting the hydrogenation the treatment may involve hydrogenation to approximately one double bond in the presence of a nickel hydrogenation catalyst followed by completion of the saturation in the presence of a platinum or palladium catalyst.

The catalyst, as powdered nickel, may be prepared in any usual manner, as by oxidation and then reduction, and will desirably be supported on a suitable support as kieselguhr, pumice, or the like.

Further, in proceeding in accordance with the invention the methyl abietate may be isomerized, as for example, by heat treatment or by treatment with chemical reagents, as sulphuric acid, hydrochloric acid, etc., before hydrogenation.

The methyl abietate may be prepared by heating methanol and rosin (abietic acid) at a temperature of about 225 C.-290 C. under a pressure of about 1200-2000 lbs. without use of a catalyst, 01' by autoclaving methyl chloride with sodium abietate in solution in a solvent, as ethyl, methyl or butyl alcohol, or otherwise.

As illustrative of the hydrogenation of the 45 methyl abietate, for example, a quantity of methyl abietate is agitated with about 1.5% of a powered nickel hydrogenation catalyst for two hours at a temperature of about 185 C. while introducing hydrogen under a pressure of about 40 atmos- The product will be about 65% saturated with hydrogen. Similarly the hydrogenation may be effected at a temperature of about 150 C. while introducing hydrogen under a pressure of about 200 atmospheres. The product will be highly saturated, being over 80% saturated.

As illustrative of the practical adaptation of the method of this invention where partial saturation is accomplished in the presence of a nickel catalyst followed by further saturation in the presence of a platinum catalyst, for example,

methyl abietateis treated with hydrogen under a pressure of'about 20 atmospheres at a temper-,

ature of about 165- C. while being agitated vigorously with about 2 of powdered nickel hydrogenation-catalyst. -The treatment is continued for about three-quartersof an hour and a productsaturatedto about 55% is obtained. The partially saturated methyl abietate is then treated with hydrogen at a temperature of about 30 C. and under a pressure of about 100 atmospheres in the presence of a platinum catalyst, effecting more complete saturation.

If desired the methyl abietate may be passed with hydrogen over a stationary nickel hydrogenation catalyst, having an activated surface prepared by oxidation and reduction, under the temperature and pressure conditions indicated until partially saturated, and then over a-stationary platinum catalyst, under the temperature and pressure conditions indicated, until the desired percentage of saturation is obtained.

If desired, the methyl abietate may be hydrogenated in the vapor phase by passing its vapors together with hydrogen over an activated nickel or platinum catalyst. In vapor phase hydrogenation thev methyl abietate will be heated to say 50 C. to 350 C. undera pressure of say-1-'760 mm. mercury to vaporize it and will be passed over the nickel catalyst with hydrogen at a temperature of say 150 C.-225 C. and under the same pressure conditions.

When desired the methyl abietate may be isomerized, as for example, by heatingwith a small proportion of an acid, as hydrochloric acid, dilute sulphuric acid, etc. or by heating to a temperature within about the range 225 C.-300 C. and then hydrogenating.

The hydrogenated methyl abietate embodying this invention is highly advantageous as an ingredient in lacquers, since it is compatible with nitrocellulose and the various other usual ingredicuts of lacquers and will give desirable qualities to the lacquer film. As typical of its use in a lacquer, for example, a desirable lacquer may be made up on the following formula: V

7 Per cent Nitrocellulose (desirably of a viscosity of 10.0

second) -1 Hydrogenated methyl abietate 8.5 Toluene 30.0 Ethyl acetate 7.0 Butyl acetate 26.0 Butanol and ethyl alcohol 10.0 Gum damar solution 8.5

In the above formula it will be understood that various well known solvents, diluents, gums, etc. may be substituted for those specified. V

In proceeding in accordance with this invention the nickel catalyst will desirably contain some nickel oxide and may contain considerable proportions of copper, cobalt or'the like. Further, a base metal catalyst, as zinc oxide, chromium oxide, etc., etc. maybe employed. 7

In accordance with this invention it will be found that methyl abietate may be hydrogenated to the tetrahydro stage.

This application constitutes a division of they application for United States Letters Patent filed by me June 3, 1931, Serial No. 541,953.

What I claim and desire to protect by Letters Patent is:

1. A coating composition including asingredients nitrocellulose, hydrogenated methyl abietate and a solvent.

2. A coating composition including as ingredients low viscosity nitrocellulose, hydrogenated methyl abietate and a solvent.

3. A coating composition including as ingredients nitrocellulose, hydrogenated methylabietate, a gum and a solvent.

4. A coating composition including as ingredi ents nitrocellulose about 10%, hydrogenated methyl abietate about 8.5% and a solvent.

5. A coating composition including as ingredients nitrocellulose about 10%, hydrogenated methyl abietate about 8.5%, a gum and a solvent.

6. 'A coating composition including as ingredients nitrocellulose, methyl abietate, which has been isomerized and then hydrogenated and a solvent. a t '7. A coating composition including as ingredients a hydrogenated methyl abietate the unsaturated bonds of which are about 80% saturated with hydrogen, nitrocellulose and a solvent.

8; A coating composition including as ingredients tetrahydro methyl abietate, nitrocellulose and a. solvent. 9. A coating composition including as ingredients a hydrogenated methyl abietate, the unsaturated bonds of which are about 65% saturated with hydrogen, nitrocellulose and a solvent.

IRVIN W. HUMPHREY. 

